Synthesis, structural and spectroscopic study of aromatic thioester compounds (original) (raw)
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European Journal of Chemistry, 2010
An efficient synthesis of the title compound, 1-(4-methylbenzoyl)-3-(4-aminosulfonyl phenyl)thiourea, was carried out by reaction of 4-methylbenzoyl chloride with potassium thiocyanate in acetone to afford 4-methylbenzoyl isothiocyanate in situ followed by treatment with sulfanilamide. The structure was confirmed by spectroscopic data and elemental analyses. The molecular structure was determined from single crystal X-ray diffraction data. It crystallizes in the monoclinic space group P21/n with unit cell dimensions of a = 4.8116 Å, b = 17.150(3) Å, c = 18.677(3) Å, = 96.487(4) °, and V = 1531.4(5) Å 3 .
An ab initio quantum mechanical study of thioesters
Journal of Molecular Structure: THEOCHEM, 1995
Model thioesters have been studied using ab initio quantum mechanical computations to determine the geometry and difference in energy for inherent rotamers. The Z isomer of the thioester is found to be 4.9 kcal mol-' (AC&s more stable than the E isomer, with the barrier for rotation (Z + E) 10.1 kcal mol-' (AC;,,). Parameters for molecular mechanics computations are provided.
Journal of Molecular Structure, 2010
The 1-(4-(4-Fluorobenzamido)phenyl)-3-(4-fluorobenzoyl)thiourea species (1) has been synthesized and characterized by GC-MS, elemental analyses and 1 H NMR and FTIR spectroscopy techniques. The crystal structure of the novel compound -having a benzamide moiety attached to a thiourea nucleus -has been determined by X-ray diffraction. The species crystallize in the triclinic space group P-1, Z = 4, with 2 molecules per asymmetric unit. Additionally there is one ethylacetate solvent molecule per asymmetric unit. The carbonyl and thiourea groups are almost planar and the conformation adopted by the C@S and the C@O double bonds is mutually antiperiplanar. Density functional theory methods have been applied to determine the conformational space around the central -C(O)NHC(S)NH-moiety. The vibrational properties have been studied by FTIR and FT-Raman spectroscopy along with quantum chemical calculations at the B3LYP/6-311+G Ã level of approximation.
2017
In the present work, the quantum theoretical calculations of the molecular structure of the 1-(1, 3-Benzothiazol-2-yl)-3-(thiophene-5-carbonyl) thiourea has been predicted and are evaluated using Density Functional Theory (DFT) in gas phase. The geometry of the title compound was optimized by B3LYP/6-311+G and B3LYP/6-311+G* methods and the experimental geometrical parameters of the title compound such as bond lengths (A), bond angles (°) and torsion angels (°) were compared with calculated results. The theoretical 1H and 13C NMR chemical shift (GIAO method) values of the title compound are calculated and compared with the experimental results. The computed data are in good agreement with the experimental data. Frontier molecular orbitals (FMOs) such as HOMO orbital, LUMO orbital and HOMO-LUMO energy gap, molecular electrostatic potential (MEP), electronic properties such as ionization potential, electron affinity, global hardness, electronegativity, electronic chemical potential, e...
ijdddonline.com, 2011
A series of N-p-methylbenzoyl-N' thiourea derivatives bearing different substituents have been synthesized and screened in order to evaluate for their antibacterial and antifungal activity. Antibacterial and antifungal activity of the title compounds has been evaluated by varying the substituents in the thiourea moiety. Reaction of pmethylbenzoyl chloride with ammonium thiocynate followed by the addition of various aromatic amines afforded N-pmethylbenzoyl-N' substituted thiourea. The structures of newly synthesized compounds has been supported by IR and 1 HNMR spectral analysis. Among the synthesized compounds N-(4-methylbenzoyl)-N'-(4-chloro-2-nitrophenyl) thiourea and N-(4-methylbenzoyl)-N'-(4-methylphenyl) thiourea have been found to exhibit excellent antibacterial and antifungal activity when compared with the standard drug.
Malaysian Journal of Analytical Science, 2017
Derivatives of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea were successfully synthesized from the reaction of 1,10phenanthroline with x-bromobenzoylisothiocyanate (x = ortho, meta and para) to give phen-o-BrBT, phen-m-BrBT and phen-p-BrBT, respectively. The molecular structures of the derivatives compounds were elucidated based on the crystal structure of Nbromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea, CHNS elemental analysis, mass spectrometry, spectroscopic data (infrared, ultraviolet-visible, nuclear magnetic resonance and luminescence) and cyclic voltammetry.The mass spectrum show similar m/z values at 460.9 and 260.0, which represent the molecular ions for [(phen-x-BrBT)-Na] + and [BrBT] + , respectively. The presence of a v(NH) (3389-3599 cm-1) and the disappearance of ν(NH 2) bands from 1,10-phenanthroline-5-amine indicate the formation of the N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea. Attachment of a Br atom to the benzoyl moiety reduced the stretching frequency of C=O group by >20 cm-1 compared with phen-BT ligand. The compounds exhibit two π→π* bands at 231 and 269-270 nm for the phenanthroline and benzoyl moieties, respectively. The resonance for N-H proton appeared at δ = 11.53-12.49 ppm. In addition, 13 C resonance signals for C=S and C=O groups were recorded at around 182 and 167.39-169.08 ppm, respectively. The synthesis and effect of a Br substitution on the structural and luminescence properties of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea derivatives are presented and discussed in this study.
Central European Journal of Chemistry, 2010
Four novel thiourea derivatives containing a thiazole moiety were synthesized and characterized by IR, 1H and 13C NMR, mass spectrometry and elemental analysis. The crystal structure of 1a was determined from single crystal X-ray diffraction data. It crystallizes in monoclinic space group P21/n with unit cell dimensions a = 11.7752(6) Å, b= 3.8677(2) Å, c= 27.4126(13) Å and β = 92.734(5) Å. There is a strong intramolecular hydrogen bond of the type N-H⋯O, with H⋯O distance of 2.5869(19) Å. The mass fragmentation pattern has also been discussed. The antifungal activity of the synthesized compounds was studied by broth micro-dilution method and poisoned food technique. The compounds 1b and 1c possessed a broad spectrum of antifungal activity.
Turk J …, 2010
Synthesis of some novel 1-(3,4,5-trimethoxy)benzoyl-3-arylthiourea derivatives (1a-o) was accomplished in 2 steps. The synthetic route involves the reaction of 1-(3,4,5-trimethoxy)benzoyl chloride with potassium thiocyanate in 1:1 molar ratio in acetone to afford the corresponding isothiocyante followed by treatment with suitably substituted anilines. The structures of the products were established by elemental analyses, IR, 1 H-and 13 C-NMR, and mass spectroscopy and for 1b and 1m from single crystal X-ray diffraction data.